Fourth Time's the Charm
by Zephyr Hearts
Summary: Triles; To be exact they have had sex three times, but to Miles this is his first time. /Rated M for fluffy smut/ Beta-reader: Amethyst Beloved.


A/N: I wrote this around Valentine's Day. It's a fluffy/smutty one-shot for Triles :) Enjoy!

Disclaimer: I don't own Degrassi, only my story :D

Thank you so much to **Amethyst Beloved** for beta-reading my story :) I'm forever grateful! Thank you so much for helping me make my story better with your lovely comments! This is for you :)

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 **\+ Fourth Time's the Charm +**

"Wow, they weren't kidding when they said it was going to storm tonight." Tristan muttered as he stared blankly out the window of Miles' bedroom. His boyfriend had just walked out of the shower, a navy blue towel wrapped loosely around his hips. Tristan turned around, looking away from the raging storm outside.

His eyes danced over his lover's half naked body. Miles' ran a towel over his hair and tossed the damp cloth into the laundry basket. He walked over to the chest of drawers and reached into the bottom drawer, pulling out his favorite pajama pants. Miles peaked over his shoulder, making sure that Tristan was watching him and he let the towel drop from his waist to the floor. Tristan bit his lip as Miles pulled his pajama pants on with nothing underneath.

"Since when do you go commando?" Tristan asked as he removed his own shirt and climbed into the bed.

"Since I ran out of clean boxers. I need to do laundry tomorrow." Miles answered as he turned the light off in his room and climbed in his bed with Tristan.

The dark haired teen jumped when a loud clash of thunder followed after a bright flash of lightning. Miles tried not to laugh as he made himself comfortable on the mattress. He lifted his arm and Tristan quickly cuddled close to his boyfriend. Miles ran his fingertips up and down Tristan's back, just along his spine. Tristan hummed in approval and listened to the loud patter of rain against the window.

They were silent for minutes before Miles spoke. "Can I get a goodnight kiss?"

Tristan tilted his head up. "A kiss, and that's it."

"I won't make any promises." Miles cupped Tristan's cheek and kissed him. Tristan attempted to pull away before the kiss could grow any deeper. He knows how persuasive the brunette can be, even if it was just a simple kiss and he knows how he gets when they're alone, in the bed together. The last time it was supposed to be a "kiss goodnight" they were at Tristan's place, his parents were downstairs, and Miles had wanted a kiss from him before they went to bed, and that kiss had turned into a hot steamy make out session that lead into a steamy blow job in the shower. Tristan loved how forward Miles could be, he wasn't complaining the least bit.

Miles reached around, placing his hand on the back of Tristan's head, locking his lips together harder. The green eyed boy moaned in the kiss as he gently nipped on Tristan's pouty bottom lip, coaxing his mouth open.

Tristan gave in. He parted his lips to Miles and both sighed as their tongues touched. Miles massaged his tongue with Tristan's before taking the wet muscle between his teeth and sucking gingerly on it. Tristan groaned in his throat and pulled away when he felt Miles' hand move to his hip.

"Miles David Hollingsworth, what do you think you're doing?" Tristan questioned.

"Mmm, I love it when you call me by my full name." Miles ignored his question.

Tristan resisted the urge to roll his eyes. Miles leaned forward and he began peppering kisses on Tristan's neck. The dark haired teen sighed and tilted his head to the side giving Miles more access to his flesh. Miles grinned inwardly, he enjoyed how easily Tristan can fall limp into his arms. Tristan reached up gripping the hair on the back of Miles' head and realized it was still pretty damp.

Miles removed his lips from Tristan's neck and kissed him brusquely on the lips.

"Do you want to have sex?" Miles asked.

Tristan was taken aback from Miles' forward question.

It wouldn't have been their first time, as they have had sex before, only three times to be exact. The first time Tristan was a nervous wreck, because it was indeed his first time, but it was also Miles' first time with a boy, it was weird (but in a good way) for the both of them. The second time they were on school property (on the roof), that time Tristan started it, Miles finished it, and the third was on top of Miles' convertible.

They were getting "better at it" to say the least. All those times Miles had always beat around the bush about sex. They would just make out and one thing would lead to another. He never really asked, not like now.

"Yes, no?" Miles asked.

"I'm just… it surprised me." Tristan smiled.

"Figured I'd ask this time. Make it more comfortable for you. You don't have to say yes just because I asked," Miles said as he placed a small kiss on the tip of Tristan's nose.

Tristan fought the urge to break down and sob like a little girl. Miles had always found a way to make Tristan fall in love with him over and over again. The fact that he asked to make Tristan feel comfortable made butterflies flutter in the pit of his stomach; it meant that Miles cared about his feelings and he couldn't say no, he answered Miles with a kiss.

Tristan deepened the kiss by chewing softly on Miles' bottom lip, earning himself a low moan as Miles opened his mouth to his boyfriend. He moved so he was laying on top of Tristan, and the boy beneath him opened his legs to brunette. Tristan tilted his head, trying to get a better lip lock with his boyfriend as their kiss became sloppy and needy.

Miles broke the lip lock and he showered Tristan's chest with soft kisses. Tristan sighed loud when he felt Miles' tongue on his nipple. The brunette swirled his tongue along the hardening bud before he enveloped his lips around it. Miles tugged on Tristan's nipple between his teeth before kissing his way down.

A flash of lightning outside illuminated Miles' bedroom and Tristan caught a glimpse of his boyfriend sucking on his hipbone. Miles alternated between licking and biting, making sure he brought the blood to the surface, creating a deep red love bite. Miles ran his hands up Tristan's quivering thighs and grabbed his pajama pants before slowly tugging them down, throwing them to the floor.

Tristan whimpered when Miles wrapped his lips around his length. There had only been a couple of times where Miles gave Tristan a blow job, both times Tristan had asked Miles if he was comfortable with it, and of course Miles said yes, despite how scared he was, Miles always wanted to make Tristan feel good.

Tristan could tell that Miles had gotten the hang of it. The way Miles used his tongue, teeth and lips over his cock made Tristan fall apart on Miles' bed. The green eyed boy reached up and cupped Tristan's balls in his hand, making the boy beneath him cry out.

Miles wrapped his lips around Tristan's hard length, hallowing his cheeks as he sucked hard.

"Fuck, Miles." Tristan sighed.

Miles moved his head down, forcing his throat open and gagged as the tip of Tristan's hard length touched the back of his throat. He gently massaged his balls all the while sucking and licking the cock in his mouth. Saliva dribbled out of his parted lips, Miles moved away and licked the chain of saliva hanging from his lip, connected to Tristan's length.

The brunette placed wet, open mouth kisses up Tristan's body, he sucked on his nipple before kissing Tristan's quivering lips.

"You've gotten better at that." Tristan stated.

Miles couldn't help the blush that flushed his cheeks. "I've been practicing." He muttered shyly.

Tristan sat up, making Miles nearly fall off the bed.

"On what, on _who_?" Tristan grimaced.

Miles chuckled. "Tristan, calm down… I just did research and used some… stuff to test my gag reflex."

Tristan arched his eyebrow.

"What kind of _things_?" Tristan was curious at this point.

Miles moved to sit cross legged on the mattress. His hard-on was fading at this point, but he figured because he brought it up, he knew Tristan would ask questions, he would tell him.

"I've been eating a lot of popsicle's. Though the cold isn't very pleasant, it's helped numb and relax my throat." Miles explained.

Tristan nodded and his eyes drifted away, imagining Miles eating a popsicle made his throat dry and he swallowed hard.

Miles leaned forward and he moved to sit in Tristan's lap.

"The rain stopped." Miles muttered, starting a new conversation.

"So it did." Tristan answered.

He wrapped his arms around Miles' waist and pulled him close. The brunette linked his arms around Tristan's neck and kissed him. Normally it would be Tristan in his lap, kissing him hesitantly and sometimes animalistically, but Miles wanted to change things up for them. He was always the one to be in control of their sexcapades, he wanted Tristan to make him feel good this time.

Miles leaned back, taking Tristan with him and he gasped when his back came in contact with the bed. Tristan cupped Miles' cheek and broke the kiss.

"Tristan." Miles sighed as the dark haired teen began biting and kissing his neck. Miles reached up and gripped the hair on the back of Tristan's head. He whimpered when his boyfriend sunk his teeth on the pulse point. Tristan sucked on the rapidly beating vein, relishing the soft mewls Miles spilled into his ear; the blood rushed down to Tristan's cock, causing it to grow harder.

"Tristan, I want you to fuck me this time." Miles whispered shyly in Tristan's ear. Tristan pulled away from Miles' neck to look into his deep green eyes.

"What?" he asked.

"I want you to fuck me. I want to feel you inside me, I want to know how good it feels… I want to know what it feels like for you." Miles said.

Tristan rubbed Miles' cheek with his thumb.

The clouds outside had moved across the moon, the beams illuminated Miles' bedroom. And, for a brief moment when the beams hit Miles' face, Tristan couldn't help but think how beautiful he looked laying beneath him. Miles had always been beautiful to Tristan, despite his boyfriend's needy command to call him handsome all the time. Miles' lashes cast a light shadow on his cheeks when he closed his eyes, he sighed shakily, obviously nervous about everything that was to come. Miles never bottomed for Tristan, but knew how much he wanted to do that for him.

"Okay." Tristan whispered. He kissed Miles and slowly pushed his tongue passed his teeth. Miles kissed him back with the same overflowing passion. Their tongues wrestled for dominance, Tristan winning due to Miles' nervousness overcoming his body.

"I'll be gentle, I promise." Tristan said gently.

Miles nodded and watched as Tristan kissed down his body. When the dark haired teen reached Miles' pajama pants, he was a little disappointed to see that he was only half hard, but that would change quickly. Tristan pulled Miles' pants down and Miles lifted his butt up to help Tristan remove his sleepwear and it was tossed carelessly to the floor. Miles watched through half lidded eyes and Tristan took his semi-hard length between his lips. His mouth was so warm and soft, it didn't take his cock long to harden to its full length. Tristan sucked at the tip before swirling his tongue around the now swollen head. Miles sighed loud, his hips twitched when Tristan took more of his cock.

Tristan pulled his head back to run his lips along the soft skin of the shaft before taking one of Miles' balls into his mouth, gently sucking on it. Miles arched his back and bit his bottom lip. The things Tristan could do to him always surprised him and he enjoyed it. Tristan placed his hands on the back of Miles' thighs, pushing them to his chest.

"Tristan what are you—" Miles was cut off with his own whimper when Tristan licked his ass.

"Tristan don't— _ahh_." Miles bit his lip as Tristan swirled his tongue around the tight ring of muscle. Miles wasn't so much inexperienced on this part, he had done this to many girls and Tristan as well, but never expected to feel this good, especially to him. He dug his head into the mattress when he felt the tip of Tristan's tongue enter him so slightly. Tristan thrust his tongue in and out slowly and reached up to stroke Miles' leaking cock.

Miles groaned, his hips twitched as Tristan continued his ministrations on his ass. It was weird, but it felt so good, he didn't want him to stop.

"Miles, I'm going to use my fingers now, I'm going to warn you now it will hurt, but it's more of a burning sensation and it will get better with time." Tristan said.

Miles only nodded. He knows how much it hurts, he was told countless times. He braced himself when he heard Tristan begin sucking on his own fingers. Tristan moved up so he was on top of Miles.

"Ready?" Tristan asked as he placed the tips of his middle and ring finger at Miles' entrance. Miles nodded and inhaled sharply when Tristan slipped his fingers inside him. The feeling was so foreign to him and he wondered how long he would last before he begged Tristan to pull his fingers out. Tristan whispered soothing words into Miles' ear, coaxing him to relax.

Miles clenched the bed sheets and his jaw, grinding his teeth together. Tristan pumped his fingers slowly in and out of Miles' tight ass, making sure not to hurt him in any way. Miles' body soon began to relax as Tristan continued to slowly thrust his fingers. The pain had subsided to pleasure and Miles was biting his lip to silence the noises threatening to escape his mouth.

"I'm going to go deeper now." Tristan warned him.

"Okay." Miles said through his heavy breathing. Tristan's finger searched for a specific bundle of nerves and when he heard a loud moan erupting from Miles' throat, followed by a scream, Tristan knew he had found his boyfriend's prostate.

"Does that feel good?" Tristan purred.

"Yes." Miles sighed, "Oh god."

Miles had always heard how Tristan reacted when he rubbed his prostate. He was surprised at the noises he was making, it felt so good, and he wondered what it would feel like with Tristan's cock hitting his sweet spot rather than his fingers. The image in his head cause his cock to twitch uncontrollably and to leak more precum. Tristan rubbed Miles' prostate in an agonizingly slow circle, loving the noise his boyfriend was making.

Miles whimpered from the loss when Tristan pulled his fingers out.

Tristan moved back to the nightstand drawer where Miles kept his stash. He pulled a condom out and a small bottle of lubricant. Miles watched Tristan roll the condom on his length and pour a small amount of lube on his palm. Tristan stroked his cock before rubbing the remainder of the oil on Miles' ass.

Tristan climbed over Miles and kissed him. Miles' eyes snapped open when he felt the tip of Tristan's cock at his entrance.

"Tristan—

"Don't worry, I promised I'd be gentle." Tristan said softly. Miles clenched Tristan's biceps and bit into his shoulder when Tristan slipped the tip of his cock inside. He absentmindedly clenched his ass, giving Tristan no access to entering him more.

"Miles, just relax. I know it hurts." Tristan whispered. He hissed when Miles bit into his shoulder harder, which broke the skin just barely. Miles relaxed his body and dropped his mouth from Tristan's flesh when he tasted blood. Tristan slowly thrust his hips, sliding just the tip of his cock in and out.

When Tristan felt Miles begin to relax more and more, he pushed his cock in deeper with a struggle.

"Fuck, you're so tight." Tristan groaned.

Miles grinned shakily, then screamed when his boyfriend thrust the rest of the way inside him. His fingernails dug into Tristan's biceps, creating half moon marks on his flesh. Tears pricked at the corners of Miles' eyes and streamed down into his hairline.

"It hurts." he whimpered.

"I know, it gets better." Tristan kissed his boyfriend's tears in attempt to soothe him. Miles adjusted himself underneath Tristan. He felt so full and so stretched, it felt good, but the pain was excruciating at the same time; it felt like he was being torn in half. Miles lay there limp on the mattress trying to adjust to the member shoved up his ass, Tristan reached down and wrapped his fist around Miles' aching cock. Miles inhaled sharply and bit his lip when Tristan started to move ever so slowly.

Tristan stroked Miles' cock just as slow, trying to make him feel comfortable. Miles had done the same for him on their first time, so of course Tristan would do the same for him. Miles' lips parted, a small whimper escaped his throat and his body had started to relax.

"Fuck." Miles swore.

"Does it hurt? Do you want me to stop?"

"No, faster." Miles begged.

Tristan obliged, he thrust his hips faster and stroked his boyfriend's dick at the same pace. Miles let out a bitten off moan, his teeth digging into his bottom lip. Tristan moved his hand away when Miles reached up and pulled Tristan down to him.

"Kiss me." The brunette breathed out.

Tristan planted his lips over the other boys and moved harder, his hips slammed into Miles' own creating a loud slapping noise. Miles screamed in Tristan's mouth and squeezed his eyes more shut.

"Sorry, did that hurt?" Tristan asked when he broke the small kiss.

"No, do that again, it felt so good." Miles answered.

Tristan continued thrusting his hips hard, he was rewarded with another screaming moan; Tristan had found his prostate. He continued hitting that spot with his forceful thrusts. Tristan had Miles practically sobbing from how good it felt.

Miles would have never thought this felt as good as it did. Tristan had always told him that every time they did have sex, but words are just words right? It felt amazing and he would bottom for Tristan more often just to feel that pleasure again and again. The noises spilling from Miles' lips let Tristan know that he was close. Tristan moved faster and harder, making sure to hit his boyfriend's prostate all the while.

Miles wrapped his arm around Tristan's neck, pulling him down for a sloppy kiss. Tristan could feel Miles' insides clench around him and he came with a low moan. Miles didn't even touch his cock, he came just from Tristan's hard thrusts, his cum spilled all over his stomach. Tristan slumped over Miles and placed small kisses on his cheek, his temple and his forehead.

"That was so good." Miles winced when Tristan pulled out of him. He watched his boyfriend discard the condom in the bathroom. Tristan walked out of the bathroom with a hand towel. He wiped up the cum on Miles' stomach and tossed the towel to the other side of the room. Tristan helped Miles back up to top of the bed and climbed in next to him.

"I love you." Tristan said.

Miles smiled weakly and kissed him chastely. "I love you too."

"Maybe you should bottom for me more. There are other positions I would like to try." Tristan purred.

"Yeah, sounds good." Miles answered tiredly. He cuddled into Tristan's chest and immediately fell asleep.

Tristan kissed the top of Miles' head and closed his eyes to sleep as well.

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Reviews are greatly appreciated, flames will be promptly ignored.


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